Chemistry Research, by Faculty Member
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The Hilmey Research Group: (From left) Jacob Donius ('11), Dr. David Hilmey, Xavier & June Hilmey, Deena Butryn ('12), Nick Sylor ('11), & Mark Ghassibi ('11).
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Methodological Development and Total Synthesis of Tropanes
Our focus is on the development of chemical reactions to improve our ability to gain medicinally relevant molecules or decrease the impact of chemical synthesis on the environment. To this end, we plan to develop new synthetic methodology focusing on the consistent, mild, and “green” cycloaddition of 3-hydroxypyridines with various dipolarophiles to generate tropane systems. In addition, the [3+2] dipolar cycloaddition to 3-hydroxypyridine will be used as the central building block to synthesize the tropane natural product ferruginine in the shortest synthesis of this neurological agent if complete. Following these successful developments, our original two contexts will be merged to create a tropane library based on the natural product’s structure and conformation, leading to evaluation for biological function.
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The students working on this project—Shivani Sharma and Nick Sylor—have been able to show that the central cycloaddition reaction works with a variety of substrates and can proceed in water. We hope to make the reaction more general in aqueous solution and delve further into its mechanism using computational models.
Natural Product Isolation
Our research also includes the isolation of biologically active organic structures by working with Native Americans and their traditional medicines. Specifically we will work with the Seneca Nation of Indians and focus on plants, medicines, and their preparation to isolate and identify new organic molecules. Currently we are extracting and attempting to isolate components of sassafras and mullein which have been used in traditional Iroquois medicine for many generations. We plan to develop a joint venture to better understand the science behind what Senecas have already known for thousands of years and use this information for the chemistry education of Bonaventure students, local grade and high schools, and the Seneca Nation. Finally, we will utilize a shared approach to identify biologically potent component(s) for medicinal activity from within these traditional medicines.
The students working on this project—Sarah Morris, Pooja Desai, Shivani Sharma, and Shawn McGranaghan—have extracted the organic components of sassafras root and isolated the major organic constituent. They have also extracted the organic components of sassafras leaves and smoke derived from the mullein plant.
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In the Chem Research Lab: Sarah & Shivani seek the chemical basis for the medicinal value of mullein leaves. (QuickTime is required to view the video.)
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In the movie to the left, Sarah Morris and Shivani Sharma perform an experiment that mimicks the smoking of mullein leaves. As the leaves burn, the smoke is vacuumed up through the tubing and then bubbled through organic solutions. The smoking of mullein leaves is a traditional Seneca treatment for asthma and painful earaches. Our students are attempting to isolate the organic components of mullein smoke to understand the scientific basis for its medicinal action.
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Members of the Hilmey Group enjoy some down time at the group picnic in May 2011.
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Highlights from Conferences
Rochester Academy of Science Fall 2011 Scientific Papers Day: David Samuel ('12) presented his research, performed in Dr. Hilmey's lab, to a group of faculty and students from Western and Central New York at the RAS Fall 2011 Scientific Papers Day on Oct. 29. Samuel's talk, “NMR Characterization and Mechanistic Implications of Singlet Oxygen Addition to the Vitamin B6 Ring”, focused on new products and intermediates of oxidation of vitamin B6.
Dr. Hilmey and his research group at the 2011 RAS conference. Seated: Kelly Morrison ('13)
and Aashish Abraham ('13). Standing: David Samuel ('12) and Dr. David Hilmey.
Dr. Ryan Rhodes, Kelly Morrision, and Aashish Abraham discuss the keynote
talk on Greenland Ice Sheet dynamics.
Rochester Academy of Science Fall 2010 Scientific Papers Day: While at St. Bonaventure, Kirsten Norrell ('10) conducted research with Dr. David Hilmey on the oxidation of vitamin B6. On November 6, 2010, Kristen presented her research at the RAS Scientific Papers Day at RIT.
Kristen describes her research on the oxidation of vitamin B6 to conference attendees.
Dr. David Hilmey and Kirsten Norrell ('10).